For what its worth, this is what I feel about Winamp.
Winamp is what I feel actually started the digital media revolution in the past. Without Winamp, I seriously doubt MP3 would be so successful in becoming the compression format for music. What Winamp does is allow our underpowered computer in the Pentium era to be able to play compressed music with what is minimal specification. Of course, when it first started out, it wasn't exactly a resource saver also. But it manage to evolve and stay with the times, cutting down on the resource it needs to decompress a MP3 file and playing it back with each version update, and also at the same time, keeping its interface minimal, making it as user friendly as possible. This allows it to be very popular and helps kick start the digital media revolution.
Winamp 3 was undoubtly a piece of sh*t that is unstable, resource hogging and very very bloated. But from what I can see from Winamp 5 (which was Justin Frankel last project before he left the company) is that they manage to shed most of the problem that was with Winamp 3 and still manage to incorporate more features into it. Even though Winamp 5 is not a very power media player, but I would still recommend it to many novice user in computer as it can be very very easy to use. I know that MC can also be easy to use, but after trying to teach my sister how to use MC for a few times, I find that MC learning curve is still quite high (which is altogether another topic).
I would be sad to see Winamp (Nullsoft for this matter) die out as they produce some of the best software around like NSIS and Winamp.
Just my 2 cents in the middle of the night......